Executive Assistant

The Aspen Group (TAG) is one of the largest and most trusted retail healthcare business support organizations in the U.S. and has supported over 20,000 healthcare professionals and team members at more than 1,300 health and wellness offices across 48 states in four distinct categories: dental care, urgent care, medical aesthetics, and animal health. Working in partnership with independent practice owners and clinicians, the team is united by a single purpose: to prove that healthcare can be better and smarter for everyone. TAG provides a comprehensive suite of centralized business support services that power the impact of five consumer-facing businesses: Aspen Dental, ClearChoice Dental Implant Centers, WellNow Urgent Care, Chapter Aesthetic Studio, and AZPetVet. Each brand has access to a deep community of experts, tools and resources to grow their practices, and an unwavering commitment to delivering high-quality consumer healthcare experiences at scale.

We are seeking a highly organized and proactive Executive Assistant to provide dedicated support to senior leadership within our organization. Located in our corporate headquarters in Chicago, this role is critical in managing complex schedules, streamlining communication, and ensuring the seamless operation of executive functions both within and beyond the office environment.

The ideal individual will demonstrate impeccable attention to detail, sound judgment, and have the ability to be resourceful and proactive in anticipating the needs of executives.

Essential Responsibilities

• Serve as the primary liaison between senior leadership and internal teams or external stakeholders
• Manage several dynamic executive calendars, ensuring all logistical details are managed seamlessly.
• Plan and manage comprehensive travel arrangements, including flights, accommodations, transportation, and itineraries; maintain accurate records of travel schedules and preferences to streamline future planning.
• Draft professional and polished communication for various audiences on behalf of senior leadership when appropriate.
• Assist in the preparation of internal and external reports, presentations and other business documents, ensuring clarity, grammatical accuracy, and alignment with organizational branding.
• Process accurate and timely expense reports. Monitor expenses and liaise with finance teams to ensure compliance with policies and resolve discrepancies when necessary.
• Provide administrative support for special projects, including planning, coordination, and follow-up on deliverables.
• Assist with preparation for board meetings, executive retreats, and other high-level events, ensuring all materials are ready and logistical details are confirmed.
• Anticipate challenges and identify creative solutions; address urgent issues or requests from senior leadership with a resourceful and solutions-oriented approach.

Requirements/Qualifications

• Bachelor’s degree in business administration, communications, or a related field preferred.
• 8 years of experience providing high-level administrative support, with at least 3–5 years supporting executives or senior leadership.
• Experience coordinating executive-level travel, both domestic and international
• Knowledge of basic financial processes, such as preparing expense reports and managing budgets.
• Advanced proficiency using Microsoft Office Suite and collaboration tools (e.g., Teams, Google Meet).
• Exceptional organizational and multitasking skills with the ability to prioritize effectively.
• Strong written and verbal communication skills, including the ability to draft polished and professional correspondence.
• Ability to use discretion and handle sensitive/confidential information with the highest level of professionalism.
• Experience working in a corporate, complex, or dynamic organization is a plus.

Annual Pay Range: $85-110k, plus bonus opportunity

A generous benefits package that includes paid time off, health, dental, vision, and 401(k) savings plan with match

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